.ALPHA.-LAPACHONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H14O3
Molecular Weight	242.2699
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)CCC2=C(O1)C(=O)C3=CC=CC=C3C2=O

InChI

InChIKey=PJWHOPKRRBUSDH-UHFFFAOYSA-N

InChI=1S/C15H14O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-6H,7-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C15H14O3
Molecular Weight	242.2699
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19924086 | https://www.ncbi.nlm.nih.gov/pubmed/11008131 | https://www.ncbi.nlm.nih.gov/pubmed/24530030 | https://www.ncbi.nlm.nih.gov/pubmed/11501791

The bioactive quinone Alpha-lapachone was originally isolated from the heartwood of trees of the Bignoniaceae family (Tabebuia sp). It can also be found in other families such as Verbenaceae, Proteaceae, Leguminosae, Sapotaceae, Scrophulariaceae, and Malvaceae. Alpha-Lapachone showed potent cytotoxicity against different cancer cell lines. Alpha-lapachone is an "irreversible" inhibitor of topoisomerase II. Alpha-lapachone demonstrated antibacterial activity against pathogenic organisms Staphylococcus aureus and Salmonella typhi and antifungal activity against Candida albicans and Trichophyton mentagrophytes.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cystathionine gamma-synthase 1 Target ID: Q1M0P5 Gene ID: NA Gene Symbol: metB Target Organism: Helicobacter pylori (Campylobacter pylori) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17981822	Inhibitor 8504		11.0 µM [IC50]
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11320661 \| https://www.ncbi.nlm.nih.gov/pubmed/11008131	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Wound infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16553949	Curative		Preclinical	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24530030	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.	2014-03-01	24530030
The trypanocidal activity of naphthoquinones: a review.	2009-11-10	19924086
Enzymatic characterization and inhibitor discovery of a new cystathionine {gamma}-synthase from Helicobacter pylori.	2008-01	17981822
Tabebuia avellanedae naphthoquinones: activity against methicillin-resistant staphylococcal strains, cytotoxic activity and in vivo dermal irritability analysis.	2006-03-22	16553949
Inhibitory effects of lapachol derivatives on epstein-barr virus activation.	2003-02-20	12538012
Activity of natural and synthetic naphthoquinones against Toxoplasma gondii, in vitro and in murine models of infection.	2002-09	12375370
Radermachera xylocarpa: the highly efficient source of lapachol and synthesis of its derivatives.	2001-08-15	11501791
Novel mechanism of cellular DNA topoisomerase II inhibition by the pyranonaphthoquinone derivatives alpha-lapachone and beta-lapachone.	2001-03	11320661
Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives-eleutherin, alpha lapachone, and beta lapachone.	2000-11-01	11008131
Effects of beta-lapachone, a peroxide-generating quinone, on macromolecule synthesis and degradation in Trypanosoma cruzi.	1985-07	2409922

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

1 uM alpha-lapachone failed to inhibit Trypanosoma cruzi epimastigotes DNA synthesis or the parasite growth in vitro, which suggests that inhibition of DNA synthesis was essential for beta-lapachone action on cell division and growth.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:50:23 GMT 2025` Edited by `admin` on `Mon Mar 31 21:50:23 GMT 2025`
Record UNII	VPE3AOX9QV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-26327

Preferred Name

English

.ALPHA.-LAPACHONE

Common Name

English

NSC-629747

Code

English

2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE, 3,4-DIHYDRO-2,2-DIMETHYL-

Systematic Name

English

ALPHA-LAPACHONE

Common Name

English

Code System Code Type Description

NSC

629747